CHEBI:28193 - lupanine

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ChEBI Name lupanine
ChEBI ID CHEBI:28193
Definition The δ-lactam obtained by formal oxidation at the 2-position of sparteine. The major alkaloid from the seeds of Lupinus exaltatus, L. mexicanus and L. rotundiflorus, it is among the most important of the tetracyclic quinolizidine alkaloids.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:6569, CHEBI:545432, CHEBI:25081
Supplier Information
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Formula C15H24N2O
Net Charge 0
Average Mass 248.36390
Monoisotopic Mass 248.18886
InChI InChI=1S/C15H24N2O/c18-15-6-3-5-14-11-8-12(10-17(14)15)13-4-1-2-7-16(13)9-11/h11-14H,1-10H2/t11-,12-,13-,14+/m0/s1
InChIKey JYIJIIVLEOETIQ-XDQVBPFNSA-N
SMILES [H][C@]12CN3CCCC[C@@]3([H])[C@]([H])(CN3C(=O)CCC[C@]13[H])C2
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing lupanine (CHEBI:28193) has parent hydride sparteine (CHEBI:28827)
lupanine (CHEBI:28193) is a δ-lactam (CHEBI:77727)
lupanine (CHEBI:28193) is a quinolizidine alkaloid (CHEBI:26515)
lupanine (CHEBI:28193) is a tertiary amine (CHEBI:32876)
lupanine (CHEBI:28193) is conjugate base of lupanine(1+) (CHEBI:64261)
Incoming 13-(2-methylcrotonoyloxy)lupanine (CHEBI:18360) has functional parent lupanine (CHEBI:28193)
13-hydroxylupanine (CHEBI:18328) has functional parent lupanine (CHEBI:28193)
17-hydroxylupanine (CHEBI:64287) has functional parent lupanine (CHEBI:28193)
lupanine(1+) (CHEBI:64261) is conjugate acid of lupanine (CHEBI:28193)
IUPAC Name
spartein-2-one
Synonyms Sources
(+)-2-oxosparteine ChEBI
(+)-Lupanine KEGG COMPOUND
(7alpha,7aalpha,14alpha,14abeta)-dodecahydro-7,14-methano-2H,11H-dipyridol[1,2-a:1',2'-e][1,5]diazocin-11-one ChEBI
2-oxosparteine ChemIDplus
d-lupanine ChEBI
lupanine ChEMBL
Lupanine KEGG COMPOUND
Manual Xrefs Databases
C00002225 KNApSAcK
C10772 KEGG COMPOUND
CPD-8917 MetaCyc
View more database links
Registry Numbers Types Sources
550-90-3 CAS Registry Number KEGG COMPOUND
550-90-3 CAS Registry Number NIST Chemistry WebBook
550-90-3 CAS Registry Number ChemIDplus
86318 Beilstein Registry Number Beilstein
86318 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11045450 PubMed citation Europe PMC
11714325 PubMed citation Europe PMC
17269069 PubMed citation Europe PMC
17402058 PubMed citation Europe PMC
19467626 PubMed citation Europe PMC
20580181 PubMed citation Europe PMC
7810174 PubMed citation Europe PMC
930514 PubMed citation Europe PMC
9751462 PubMed citation Europe PMC
Last Modified
28 July 2014
General Comment
2007-06-14 Confusion exists in the literature between lupinine and lupanine. Thus lupinine is a bicyclic quinolizidine alkaloid whereas lupanine has a methylene-bridged dipyridodiazocine structure containing two quinolizidine systems. Unfortunately the two terms are sometimes used synonomously.